How to Hire and Get the Most out of an EA

A Case Study

A friend and mentor, (Alex Ottewell, amazing entrepreneur in the Oil and Gas space, give him a follow on Linkedin) asked me for advice on this and I thought it might be of general interest, as well.

8 years ago I was running 3 businesses, had an office staff to do the tactical stuff for each business but I ran my own calendar and answered all of my own emails. I was stressed.

There is a part of my brain that will not reconcile the fluid and dynamic nature of a busy person's calendar, when left to my own devices I consistently get it wrong which means missed appointments, disappointed colleagues, and all the bad stuff that comes from this type of mental limitation. As we all do, I compensated for this shortcoming and I did so by doing less. I had to direct my focus to getting this part of my life functional and that just meant I had to do less so I could at least do what I said I'd do. Stupid, in hindsight, but this was my way, then.

One day a Board member of mine booked a very high-profile speaker and consultant on time management (oh, the irony!). He invited me to bring my team at his expense and told me the dates, which I promptly misremembered and booked flights and hotels for the wrong date. When we all showed up, I wasn't just embarrassed in front of my friend, but my entire team. Mortified doesn't begin to describe it. We sorted it out and I went home with my tail between my legs but determined to make a change.

I architect solutions to problems I recognize through three lenses: Mindset, Toolset and Skillset.

“We are all a part of the whole, when we heal something in ourselves, we heal it for the world.” —Fran Grace

Mindset

Every time I approach Mindset as the gateway item in a solution set, I discover headtrash that I never even knew was there. Every single time that headtrash is rooted in my Ego, in my concern about how others might perceive me, rather than the value of the work I do. The same is true for you, too.

My practice is to think about all the assumptions I’m making that simply aren’t serving me, and are creating the problem that requires a solution. Sometimes I just think through them, but sometimes I will write them out so that I can think more clearly and deeply about them. Then I play a game of “What If …"

For this exercise, I remember clearly listing out:

1. My assistant needs to be local to me, someone I can speak to face to face.

   1. But What If this person doesn’t have to be local to me, would that create more or less opportunity for a real solution to this problem?

2. I can’t afford to spend big money on an assistant who may just sit and do nothing most of the time.

   1. But What If I didn’t pay for time I didn’t use?

3. I don’t want to manage yet another employee, sinking my time into assigning and managing tasks. It’s easier to do it myself.

   1. But What If I could find someone I wouldn’t have to do that for?

In the end, with my headtrash sorted, I figured out that what I needed was not what I had been thinking I needed. Whereas I thought I needed a secretary, someone of limited intelligence to sit and process items I assigned, what I really needed was a professional Executive Assistant who could be there when I needed her, bill me accordingly, and be so good that I’d never have to tell her what to do, but she would know and just do it. A tall order but it gave me clarity and direction for my thinking.

“Surrender is the surest route to total fulfillment”

—David Hawkins

Toolset

Since I was willing to counter my own assumptions about physical presence, I was then able to look for a virtual assistant. I went to Upwork, put in a broad range of compensation, and restricted the search to native speakers who lived in the US, and in my timezone. I required a video interview and gave it 3 days to see what turned up.

My compensation range was a bit higher per hour than most people would think appropriate, but I knew I didn’t have to multiply that number by 40 hours a week. (In fact, most weeks, I get billed for 2-3 hours max, and this is the hack that’s most important to the story. Don’t’ pay for what you don’t consume, but pay very well for what you do use.)

I scheduled 12 video interviews and the first one was Gillian, a lovely person living outside DC, originally from the UK and looking for something to do for 10-15 hours per week. Every other person I talked to I kept wishing that they would answer questions like Gillian had. At the end of two days, I had my pick.

OK, I get it, you’re business is different. You run the only business on earth that needs everyone to be face-to-face to get things done. Really examine that assumption and begin to pare the things away that actually need physical input. I felt that way upfront, but found that it was worth slight tradeoffs to improve the overall picture. Sometimes I have to run an errand that an assistant should be doing, but having total control over my schedule makes that a rare thing, and one that I don’t mind. I don’t know your business, but if you hire for the right tasks, you’ll probably find you can shift those tasks to where they need to be and still benefit from a virtual person doing the work.

“It takes skill and discipline to bat away the pests of bad perceptions, to separate reliable signals from deceptive ones, to filter out prejudice, expectation, and fear. But it’s worth it, for what’s left is truth.”

— Ryan Holiday

Skillset

Finding the person, frankly, is the easiest part. Learning how to work with the person is much harder. I see so many people get hot-and-bothered about getting an assistant and then literally have no idea what to do once they’re hired. A friend of mine in the business once followed my model, hired an assistant, wouldn’t meet with her regularly, wouldn’t outline her duties, and was always mad at her for not being perfect. Not to say that people are like objects, but that’s like buying a pressure washer and being furious that your cars are dirty after you refused to hook it up to the water hose.

In our first meeting, I was candid with Gillian and said “I don’t really know how to do this, can you help me think through it?” She immediately popped in with a set of requirements that would help us get off on the right foot:

1. She said “Look, from now on, you work for me. I’ll set your schedule according to your instructions and the appointments that come in and if you follow that schedule, you’re going to love your life.”

2. Then she said “What would your ideal day look like?” Being a bit of a smartass I said “I want to show up to work at 9:30, take a two hour lunch and leave at 4:30.” She nodded and said “Done,” and I’ve lived that work schedule with very little deviation for 8 years.

3. Then she said “For 90 days, we will meet every morning at 9:15. We will review the past week, talk about the next week and make micro adjustments. After that, we will only meet when we have questions.” We did so and she learned about how I wanted her to think about the priorities in my life. She learned about my list of hatamoto (see previous post), and what I wanted to do with my time and didn’t want to do.

A month later I came home and Sheya was on the phone and seemed very focused. When she hung up I asked her who she was talking to. “Gillian,” she said, “we speak every two weeks so that I can tell her all the family things we need to have on your calendar.” I had never thought of that, Gillian took it upon herself to do it, and it made my world so much easier. I’ve never missed a game, a recital, a school play, soccer game, nothing. It’s all on the calendar and we arrange business to suit our lives, not the other way around.

As we matured our relationship, she asked for more direct control over some of the inputs in my work life. I gave her access to my Inbox which freaked me out at first but was a great decision. Now she monitors unanswered emails and prompts me when they grow too stale, or jumps right on them if they involve a request she can handle without my input. She has my credit card numbers, and is listed on all of my travel accounts and does all the things every week to deal with travel. I’ve barely booked a flight or hotel in 8 years, and when I do it’s never as good a result. (We once took the kids to stay at the St Regis in Atlanta for back-to-school shopping and we walked into a suite with a kiddle tent, teddy bears, and kid-sized robes.)

We no longer meet regulary but will have a call every 2-3 weeks to work through the backlog of requests for my time. Typically 30 minutes to an hour, but lots of that is friendly talk about our personal lives, too. Everything else is text and email, and her initiative to make calls that I very rarely question or reverse.

Does she ever make mistakes? Sure, but never fatal ones. She’s never cost me a dime that she hasn’t made up for 100x over. She did once book me on a Southwest flight, in the middle row, from Maui to Las Vegas. I haven’t forgiven her yet!

“Great opportunities never have ‘GREAT OPPORTUNITY’ in the subject line.”

— Scott Belsky

Today I’m the CEO of 8 businesses and Gillian is my EA in all of them. There is no doubt in my mind that I could do everything I do without her. At our firm Christmas Party a couple of years ago I introduced my mother, my wife, my mother-in-law, and Gillian as the most important women in my life. I wasn’t being cute, it was — and is — a true statement.

Question your own assumptions about what you think is necessary and possible and follow your concerns over the edge to find something that works for you.